Sports News Without Fear, Favor or Compromise
Sports News Without Fear, Favor or Compromise

Cracking The Case Of The Oscar Winner Who Hooked Up With Matthew Berry's Friend

Illustration for article titled Cracking The Case Of The Oscar Winner Who Hooked Up With Matthew Berrys Friend

When we last checked in, Matthew Berry's friend had gotten some strange from a Hollywood actress and it was evidently a big deal—assuming Matthew Berry has friends who look like Matthew Berry. The case was cold, until now.

Over the weekend, reader "Joe" sent a very detailed analysis with this email:

Dear Mr. Matthews:

Although you may well wish to put this case on hiatus on the grounds of sordid absurdity, or perhaps the grounds no good can possibly come of it, it is considerably less muddled than you let on in your recent Deadspin post. As far as I can tell, there are only three possibilities, one more possible than the others.

The attached analysis has been culled from the infallible sources that are Wikipedia, Box Office Mojo, People Magazine, and The Talented Mr. Roto.

Please accept a preemptive apology for wasting your time, and have a good weekend.


Well, Joe, my weekend wasn't the greatest, but thank you anyway. Here now, since it is so outrageously detailed, is Joe's complete report, in which he names who he thinks banged Matthew Berry's friend. A sic alert is in effect.

Matthew Berry recently relayed a suggestive anecdote concerning an anonymous friend hooking up with a bona fide movie star. While Berry predictably revealed no names, he has provided a number of clues in subsequent fantasy football columns, some factual and others more subjective, regarding the identity of the actress, presumably to fuel speculation and interest on the part of his readership. The device has succeeded in creating some wild and irresponsible speculation on the identity and sexual adventures of a number of well-regarded actresses. In an attempt to clear as many names as possible, let us review Berry's buddy's story. The actress is described as having won an Oscar the year before the incident and having appeared in People Magazine's 50 Most Beautiful list the year immediately following the Oscar win. In addition, the movie in which the actress earned the Oscar win was not that actress's highest grossing film; in fact, her highest grossing film came later. Berry describes his own tenure as a Hollywood writer as lasting from 1993 to 2006.The actress also reportedly invited Berry's friend, who was approximately ten years her senior, to France. Ultimately, this is all we have to go on in terms of immutable "facts," and the last of these facts are entirely useless, as we cannot nail down the age of Berry's friend or whether the actress actually travelled to France. More subjectively, the actress is described by Berry as "very beautiful" and "insanely famous," at the height of her popularity, swarmed by paparazzi, and described by Berry's friend as being somewhat lonely and open to his advances. This is also not particularly helpful. Beauty is in the eye of the beholder, and actresses are, by and large, easy on the eyes, and it should come as no surprise that nearly all of the potential actresses appear on a most beautiful list at one time or another during their careers. Fame is also largely unavoidable following an Oscar win, so it comes as no surprise that all of the eligible names are recognizable to even the most casual moviegoer.

Twenty-seven actresses have been awarded 28 Oscars for performance in the years from 1992 through 2005, which are the years which would have allowed an appearance in People Magazine's list the subsequent year, a random hook-up, and the resulting tale of debauchery all to fall within Berry's period working as a Hollywood writer. On a technicality, we can exclude the two 2005 winners from consideration, as 2005 was the last issue containing the 50 Most Beautiful (People has since expanded to a list of 100). Accordingly, the list is reduced to the following 25 candidates:

Joe's table:

Illustration for article titled Cracking The Case Of The Oscar Winner Who Hooked Up With Matthew Berrys Friend

Of the 25 Oscar winning actresses, 12 appeared in the People Magazine 50 Most Beautiful list in the immediately following year, including Emma Thompson, whose features People described as "comedic." One actress, Hilary Swank, pulled off an unprecedented double-double, creating a logical condundrum.. Of these dozen, Juliette Binoche, Helen Hunt, Jennifer Connelly, Catherine Zeta-Jones, and 2004 Hilary Swank can be immediately ruled out because their highest grossing film was not released after their Oscar-winning film. this leaves seven actresses, including 1999 Hllary Swank, who meet the factual criteria for having one an Oscar the year before appearing in the People Magazine 50 most beautiful list, during Matthew Berry's tenure as a Hollywood writer from 1993-2006. They are Emma Thompson, Susan Sarandon, Mira Sorvino, Hilary Swank, Julia Roberts, Halle Berry, and Charlize Theron. Mira Sorvino appeared to many as the odds-on favorite, and as Deadspin points out, her reputation was dragged through the mud in short order. Which may have prompted Berry to rule her out in a later article. Nonetheless amused by the interest the story had generated, Berry provided a list of semifinalists, most of whom did not meet the original criteria: 1. Catherine Zeta-Jones is immediately disqualified, as her Oscar turn was in Chicago, which was also her highest-grossing film. 2. Jennifer Connelly is immediately disqualified, as her Oscar turn was for A Beautiful Mind, which is also her highest-grossing film. 3. Halle Berry qualifies, as she won Best Supporting Actress for Monster's Ball in 2001, while X-Men: The Last Stand raked in $234,362,462 in 2006 4. Angelina Jolie is immediately disqualified as she won for Girl Interrupted in 1999 but did not make People's Most Beautiful in 2000. 5. Charlize Theron qualifies, as she won for Monster in 2003, was one of People's Most Beautiful in 2004, and Hancock grossed $227,946,274 in 2008, 6. Gwenyth Paltrow is disqualified because she won for Shakespeare In Love in 1998 but did not appear on the 1999 50 Most Beautiful List. 7. Nicole Kidman was the Academy's Best Actress in 2002 for portraying Virginia Woolf in The Hours, but was snubbed by People in 2003, perhaps for her nasal prosthesis. 8. Julia Roberts absolutely qualifies, and is probably the most likely candidate. She won for Erin Brokovich in 2000, her highest grossing film, Ocean's 11, was released the following year, and she appeared on he 2001 50 Most Beautiful List, as she always does. In addition, she is the most insanely famous actress alive and was notably in between relationships at the time. Plus, her taste in men has been, varied and interesting to say the least. 9. Juliette Binoche is a classic red herring. She is clearly not the actress in question, as she won the Oscar for Best Supporting Actress in 1996 for her performance in The English Patient, which was her highest grossing film 10. Renee Zellweger and Dame Judi Dench are both disqualfied because they won in 2003 and 1998, respectively, but failed to make the 2004 or 1999 50 Most Beautiful List. This leaves us with only Halle Berry, Charlize Theron, and Julia Roberts.

Bring it on home, Joe.

At this point, it is worth noting that it is impossible proving or disproving any of the following candidates, because there are no more facts. Similarly, it is also worth noting that it is impossible to prove the story is true in the first place, and because of this, I do not think Berry will ever name the actress or paint himself into a corner where her identity is indisputable. Nonetheless, he wants to provide enough circumstantial evidence so as to create a decisive conclusion for those with an overabundance of curiosity and free time.This leaves us with circumstantial, subjective arguments for the three finalists: Halle Berry won an Oscar with Monster's Ball in 2001, and she makes the 50 Most Beautiful list every year. Following her Oscar win, she has subsequently in a number of high-budget and high-grossing films, including the X-Men series which include her highest grossing film to date. She has been famous since the early 1990s, so you could conceivably argue that she peaked as an actress with her Oscar win. Moreover, she shares Matthew Berry's last name. However, the argument that she was at her peak in 2002 is not compelling, as Ms. Berry appears to only have become more famous and successful. Also, her candidacy is hurt by the fact that she had already been involved with Eric Benét at this point, marrying him early 2001. Monster's Ball released that December, and they remained married throughout the alloted window—although they later divorced. Also, it appears that Ms. Berry tends to be linked with rich, famous, and attractive men, which doesn't seem to help Mr. Berry's friend at all. Additionally, although current beau Gabriel Aubry speaks French, he is a Canadian. Charlize Theron is very beautiful and insanely famous , with sort of an interesting personal history. Also, she has never been married, and her highest grossing film, Hancock, came well after Monster. However, she frequently stated that she considered herself married to Stuart Townsend during her hookup window, and is also an actress whose career arc appears to be on the rise, so it'd be hard to say she peaked in 2003, Lastly, Berry wrote for Rotoworld from 1999 to 2003, and it was following this that started both and Thus, it appears his fantasy alter ego was born prior to an alleged liaison with Ms. Theron, and thus, I doubt Berry would casually describe 2004 as his old days as the Hollywood writer. Julia Roberts is as big a star as there is. She is both very beautiful and insanely famous, and is a mainstay of the 50 Most Beautiful. Her personal life is besieged by paparazzi, and has been historically known for a varied taste in men. Her highest grossing movie is Ocean's 11, which followed Erin Brockovich. Intriguingly, Julia was also transitioning from Benjamin Bratt to Daniel Moder at time, and a fling with Matthew Berry's buddy cannot be ruled out, on the basis of the factual evidence. The only quibble I might have is that I'm not sure it would be fair to describe Erin Brockovich as Roberts' peak; she is still peaking. She has been on a peak since Pretty Woman in 1993, and I don't see her in any danger of declining. In fantasy box office, she is the consensus number one pick for starting actress in a lead role and maintains yearly Oscar upside. By concluding that the most compelling answer is Julia Roberts, one hopes that Berry would abstain from passing rumors of extramarital affairs in his fantasy football column. All three actresses could be described as beautiful and famous, and it's hard to argue that anyone meeting the basic criteria is not at the height of her popularity. Nonetheless, only Julia Roberts,fits all the criteria and doesn't have any alibis.


Huh. It was quite possibly America's Sweetheart herself, the lady from Mona Lisa Smile, all along. So, does that maybe finally settle it?


Thank you for your continued support of Deadspin. We'll be back with more of the same for you tomorrow.

Share This Story

Get our newsletter